Tour Highlights
- Enjoy all three nights at Troutbeck, a stylish and historic country retreat in the heart of farm country on the New York-Connecticut border
- Bike over covered bridges, through sleepy towns, and into fertile farmland in a pastoral paradise that’s surprisingly close to New York City
- At private visits and meals, sample farm-fresh produce with local producers and meet the chefs spearheading the region’s farm-to-table renaissance in Dutchess County
- Taste artisanal whiskey and bourbon made from grains grown on the grounds of a boutique distillery
Eat
Artisan cheeses, organic greens and vegetables, maple syrup, pasture-raised beef, farm-fresh ice cream
Drink
Apple cider, local wines, and a growing network of local distilleries making hand-crafted whiskey, bourbon, and gin
As featured in:
Itinerary
Print Itinerary- Day 1
Welcome to Dutchess County
Take the train from New York City up to Wassaic or drive directly to Troutbeck, our home for the next three nights. The guest list of this historic country retreat reads like a roster of great American authors—including Twain, Thoreau, and Emerson—but feels appropriately modern, and succeeds at balancing a sense of place with all the creature comforts. We’ll get fitted to our bikes then head out for a first ride into the New York countryside. Ride the rail trail to Millerton, a sleepy little town experiencing a hip revival that’s earned it the nickname “Williamsburg on the Hudson,” where we’ll stop for lunch before biking back to Troutbeck through pastures and farm fields. Tonight we kick things off with a welcome cocktail followed by a farm-to-table dinner.
Meals: Lunch / Dinner
Destinations: Wassaic, Millerton
Accomplished: 20 miles / 32 km, elevation gain: 883 feet / 269 meters
Longer Option: 32 miles / 51 km, elevation gain: 1,983 feet / 605 meters
Accommodations: Troutbeck - Day 2
Connecticut, Covered Bridges, and Home Cooking
This morning we pedal out of Troutbeck, across the Appalachian Trail, and into Connecticut’s Housatonic River Valley. Follow the banks of the river to one of the state’s three remaining covered bridges, built in 1842. After, slip back across the New York border where a farm visit awaits us followed by lunch on the grounds. This afternoon we’ll ride through the fertile farmlands of the Tenmile River Valley, passing quaint towns like Dover Plains and Wassaic, home to a bustling art community. Back at Troutbeck, enjoy a cocktail by the pool with time to relax before dinner at our favorite local eatery.
Meals: Breakfast / Lunch / Dinner
Destinations: Kent, Wingdale, Dover Plains
Accomplished: 42 miles / 67 km, elevation gain: 2,250 feet / 686 meters
Shorter Option: 22 miles / 35 km, elevation gain: 1,094 feet / 334 meters
Accommodations: Troutbeck - Day 3
Farm-to-Table, Field-to-Glass
Today we ride north, stopping at the best local coffee shop and roaster for a truly perfect cup. Fueled up, we’ll pedal along the newest section of the Harlem Valley Rail Trail and through beautiful farm country. Lunch is fresh and hyper-local, relying on ingredients from farms in the area, followed by a visit to a nearby distillery. The Hudson Valley was once the breadbasket (and therefore also the “liquor basket”) of the young nation, where hundreds of small distilleries transformed their crops into grain alcohol. The distillery shares how it revived this tradition during a tour and tasting of their whiskeys and bourbons. Ride or transfer back to the hotel, where tonight we’ll toast at a private dinner on Troutbeck’s estate.
Meals: Breakfast / Lunch / Dinner
Destinations: Boston Corner, Ancramdale, Shekomeko
Accomplished: 25 miles / 40 km, elevation gain: 1,171 feet / 357 meters
Longer Option: 48 miles / 78 km, elevation gain: 2,398 feet / 731 meters
Accommodations: Troutbeck - Day 4
Rhinebeck
Pedal west today towards the Hudson river through the heart of horse country, with its magnificent pastures and estates. Our destination is the historic town of Rhinebeck, founded by Dutch settlers in the 17th century and home to the oldest hotel in the country. Enjoy a final lunch at a relaxed foodie restaurant before transferring back to Troutbeck to say “see you later” to the Hudson Valley. For those taking the train, your guides will bid you farewell at the Wassaic station.
Meals: Breakfast / Lunch
Destinations: Bangall, Stanfordville, Rhinebeck
Accomplished: 35 miles / 56 km, elevation gain: 2,365 feet / 673 meters
Shorter Option: 25 miles / 40 km, elevation gain: 1,540 feet / 470 meters
DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.
Arrival Details
Airport City: New York City Pick-Up Location: Wassaic Train Station or Troutbeck Pick-Up Time: 10:15 am at Wassaic Station or 10:30 am at Troutbeck
Departure Details
Airport City: New York City Drop-Off Location: Wassaic Train Station or Troutbeck Drop-Off Time: 4:00 pm
Arrival and departure details for 2025 + 2026 tours may be subject to change.
Dates + Availability
Confirm the hotels on your desired date by speaking with a Travel Specialist.
Single Supplement From: $1,250
Inclusions + Details
Accommodations
- Thoughtfully selected accommodations that reveal the true character of the region
- Luggage transfers
Meals
- Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
- 3 gourmet dinners at our favorite local restaurants and renowned culinary establishments
- Carefully selected local wine, beer, or spirits with every meal
Activities
- Wine tastings and activities as outlined in the tour itinerary
- Entrance fees to historic sites, museums, parks, and all other exclusive events
- Gratuities for baggage, porters, and hotel service
Gear
- Top-of-the-line bicycle selection
- Bike helmet
- Complimentary DuVine gear including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
- GPS in most destinations
Support
- Expert bilingual guides with extensive local knowledge
- Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
- Pick-up and drop-off before and after your tour from predetermined meeting points
- Daily bike maintenance to ensure optimal performance
